Synthesis of Novel Self-Developing Photosensitive Polyimide

Byung Hyun Ahn; Dae Woo Lee; Jin Kook Lee; Seong Soo Hong; Gun Dae Lee

Korea Polymer Journal, Vol.8, No.1, 19-25, February, 2000

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Synthesis of Novel Self-Developing Photosensitive Polyimide

Byung Hyun Ahn^†, Dae Woo Lee¹, Jin Kook Lee¹, Seong Soo Hong², and Gun Dae Lee²

Division of Material Engineering, Pukyong National University, Pusan 608-739, Korea
¹Division of Chemical Engineering, Pusan National University, Pusan 609-735, Korea
²Division of Chemical Engineering, Pukyong National University, Pusan 608-739, Korea

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Aromatic diamine monomers containing allylic ester linkage, 1,5-bis(4-aminobenzoate)-1,2,3,4-tetrahydronaphthalene (4-DABTN) and 1,5-bis(3-aminobenzoate)-1,2,3,4-tetrahydronaphthalene(3-DABTN) were synthesized through the reaction of 1,5-dihydroxy-1,2,3,4-tetrahydronaphthalene and 4-or 3-nitrobenzoly chloride. By the reaction of these diamines with pyromellitic dianhydride (PMDA) or 4,4''-(hexafluoroisopropylidene)diphthalic anhydride (6FDA), poly(amic acid)s were obtained. The inherent viscosities of the poly(amic acid)s were between 0.55 and 1.31 dL/g. the poly(amic acid)s were converted to polyimides by chemical imidization. The thermogravimetric analysis (TGA) thermograms of these polyimides showed temperatures of 5% weight loss between 323 and 389℃ in nitrogen atmosphere. The model compound, 1,5-bis(4-nitrobenzoate)-1,2,3,4-tetrahydronaphthalene (4-DNBTN), was decomposed to 4-nitrobenzoic acid and 5-(4-nitrobenzoate)-3,4-dihydronaphthalene upon addition of CF₃COOH.

[References]

Willson D, Stengenberger HD, Hergenrother PM, Polyimides, Chamman and Hall, New York (1996)
Jensen RJ, Lai JH, Polymers for Electronic Applications, J.H. Lai, Ed., CRC, Boca Raton (1989)
Kerwin RE, Goldrick MR, Polym. Eng. Sci., 2, 426 (1971)
Kubota S, Tanaka Y, Morikawi T, Eto S, J. Electrochem. Soc., 138(4), 1080 (1991)
Haba O, Okazaki M, Nakayama T, Ueda M, J. Photopolym. Sci. Technol., 10, 55 (1992)
Omote T, Yamaoka T, Polym. Eng. Sci., 32, 1634 (1992)
Ueda M, Nakayama T, Macromolecules, 29(20), 6427 (1996)
Mochizuki A, Teranishi T, Ueda M, Matsushita K, Polymer, 36(11), 2153 (1995)
Electronic and Photonic Applications of Polymers, ACS Symposium Series 218, M.J. Bowmen and S.R. Turner, Eds., ACS, Washington, D.C. (1987)
McCoy JH, Lee W, Varnell GL, Solid State Technol., 32(3), 87 (1989)
Crivello JV, Polymer in Electronics ACS Symposium Series 242, T. Davidson, Ed., ACS, Washington, D.C., 3 (1984)
Houlihan FM, Bouchard F, Frechet JMJ, Willson CG, Macromolecules, 19, 13 (1986)
Frechet JMJ, Eichler E, Stanciulescu M, Iizawa T, Bouchard F, Houlihan FM, Willson CG, Polymers for High Technology, ACS Symposium Series 346, M.J. Bowmen and S.R. Turner, Eds., ACS, Washington, D.C., 1987, pp 138-148 (1987)
Frechet JMJ, Stanciulescu M, Iizawa T, Willson CG, Polym. Mater. Sci. Eng., 60, 170 (1989)

[Referenced By]

[Related Articles]

[1] Willson D, Stengenberger HD, Hergenrother PM, Polyimides, Chamman and Hall, New York (1996)

[2] Jensen RJ, Lai JH, Polymers for Electronic Applications, J.H. Lai, Ed., CRC, Boca Raton (1989)

[3] Kerwin RE, Goldrick MR, Polym. Eng. Sci., 2, 426 (1971)

[4] Kubota S, Tanaka Y, Morikawi T, Eto S, J. Electrochem. Soc., 138(4), 1080 (1991)

[5] Haba O, Okazaki M, Nakayama T, Ueda M, J. Photopolym. Sci. Technol., 10, 55 (1992)

[6] Omote T, Yamaoka T, Polym. Eng. Sci., 32, 1634 (1992)

[7] Ueda M, Nakayama T, Macromolecules, 29(20), 6427 (1996)

[8] Mochizuki A, Teranishi T, Ueda M, Matsushita K, Polymer, 36(11), 2153 (1995)

[9] Electronic and Photonic Applications of Polymers, ACS Symposium Series 218, M.J. Bowmen and S.R. Turner, Eds., ACS, Washington, D.C. (1987)

[10] McCoy JH, Lee W, Varnell GL, Solid State Technol., 32(3), 87 (1989)

[11] Crivello JV, Polymer in Electronics ACS Symposium Series 242, T. Davidson, Ed., ACS, Washington, D.C., 3 (1984)

[12] Houlihan FM, Bouchard F, Frechet JMJ, Willson CG, Macromolecules, 19, 13 (1986)

[13] Frechet JMJ, Eichler E, Stanciulescu M, Iizawa T, Bouchard F, Houlihan FM, Willson CG, Polymers for High Technology, ACS Symposium Series 346, M.J. Bowmen and S.R. Turner, Eds., ACS, Washington, D.C., 1987, pp 138-148 (1987)

[14] Frechet JMJ, Stanciulescu M, Iizawa T, Willson CG, Polym. Mater. Sci. Eng., 60, 170 (1989)